1-phenyl-1'-methylspiro[indoline-3,4'-piperidine] | 69585-02-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-phenyl-1'-methylspiro[indoline-3,4'-piperidine]
• 英文别名: 1'-methyl-1-phenylspiro(indoline-3,4'-piperidine)；1'-Methyl-1-phenylspiro[indoline-3,4'-piperidine]；1'-methyl-1-phenylspiro[2H-indole-3,4'-piperidine]
• CAS: 69585-02-0
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: DJWYYYJXGRUKSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴化氰 、 1-phenyl-1'-methylspiro[indoline-3,4'-piperidine] 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到1'-cyano-1-phenylspiro
  参考文献：
  名称：

  Novel tetracyclic spiropiperidines. 3. 1-Arylspiro[indoline-3,4'-piperidine]s as potential antidepressants

  摘要：

  A series of 1-arylspiro[indoline-3,4'-piperidine]s was synthesized and evaluated for potential antidepressant activity by tetrabenazine (TBZ) ptosis prevention and potentiation of 5-hydroxytryptophan (5-HTP) induced head twitching in pargyline-pretreated rats. Marked TBZ activity was observed with analogues bearing an ortho substituent on the pendant aromatic ring, as exemplified by lead compound 25a, 1-(2-chlorophenyl)spiro[indoline-3,4'-piperidine], which was also very active in potentiating 5-HTP stereotypy and yohimbine toxicity, as well as in inhibiting the muricidal behavior in rats. The potent in vivo activity of 25a, coupled with weak to moderate in vitro activity with respect to the blockade of neuronal reuptake of biogenic amines, seems to suggest a profile atypical of tricyclic antidepressants.

  DOI：

  10.1021/jm00361a009
• 作为产物：
  描述：

  恩比兴 在 lithium aluminium tetrahydride 、 sodium hydride 、 lithium triethoxyaluminum hydride 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 80.5h， 生成 1-phenyl-1'-methylspiro[indoline-3,4'-piperidine]
  参考文献：
  名称：

  Novel tetracyclic spiropiperidines. 3. 1-Arylspiro[indoline-3,4'-piperidine]s as potential antidepressants

  摘要：

  A series of 1-arylspiro[indoline-3,4'-piperidine]s was synthesized and evaluated for potential antidepressant activity by tetrabenazine (TBZ) ptosis prevention and potentiation of 5-hydroxytryptophan (5-HTP) induced head twitching in pargyline-pretreated rats. Marked TBZ activity was observed with analogues bearing an ortho substituent on the pendant aromatic ring, as exemplified by lead compound 25a, 1-(2-chlorophenyl)spiro[indoline-3,4'-piperidine], which was also very active in potentiating 5-HTP stereotypy and yohimbine toxicity, as well as in inhibiting the muricidal behavior in rats. The potent in vivo activity of 25a, coupled with weak to moderate in vitro activity with respect to the blockade of neuronal reuptake of biogenic amines, seems to suggest a profile atypical of tricyclic antidepressants.

  DOI：

  10.1021/jm00361a009

文献信息

• CYCLIC AMIDE DERIVATIVE
  申请人：Okano Akihiro

  公开号：US20130203739A1

  公开（公告）日：2013-08-08

  [Problem] To provide a GPR40 activating agent having, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the salt or the compound, or the like, particularly, an insulin secretagogues and a prophylactic and/or therapeutic agent against diabetes, obesity, or other diseases. [Means of solving the problem] A compound of Formula (1): (where n is 0 to 2; p is 0 to 4; h is 0 to 3; j is 0 to 3; k is 0 to 2; a ring B is an aryl group or a heteroaryl group; X is O, S, or —NR 7 —; J 1 is —CR 11a R 11b — or —NR 11c —; J 2 is —CR 12a R 12b — or —NR 12c —; and R 1 to R 12c are specific groups), a salt of the compound, or a solvate of the salt or the compound.

  为提供一种具有GPR40激活剂作用的新化合物、该化合物的盐、盐或化合物的溶剂合物，尤其是胰岛素分泌剂和预防和/或治疗糖尿病、肥胖或其他疾病的药剂，解决问题的方法是使用Formula (1)的化合物：(其中n为0至2；p为0至4；h为0至3；j为0至3；k为0至2；环B为芳香族或杂环芳基；X为O、S或-NR7-；J1为-CR11aR11b-或-NR11c-；J2为-CR12aR12b-或-NR12c-；R1到R12为特定基团)，该化合物的盐，或盐或化合物的溶剂合物。
• NOVEL 3-HYDROXYISOTHIAZOLE 1-OXIDE DERIVATIVE
  申请人：OHKOUCHI Munetaka

  公开号：US20120277150A1

  公开（公告）日：2012-11-01

  [Object] To provide a GPR40 activating agent containing, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the compound or the salt, or the like, particularly, an insulin secretagogue and a prophylactic and/or therapeutic agent against diabetes, obesity, or other diseases. [Means of Solving the Problem] A compound of Formula (I): (where p is 0 to 4; j is 0 to 2; k is 0 to 1; a ring A is an aryl group, a heterocyclic group, a cycroalkyl group, a cycroalkenyl group, a spirocyclic group; a ring B is an aryl group, a heteroaryl group; X is 0 or —NR 7 —; and R 1 to R 7 and L are specific groups), a salt of the compound, or a solvate of the compound or the salt.

  提供一种包含GPR40激活剂的药剂，其活性成分为具有GPR40激动剂作用的新化合物、该化合物的盐、该化合物或盐的溶剂化合物等，特别是胰岛素促分泌剂和预防和/或治疗糖尿病、肥胖或其他疾病的药物。解决问题的方法是使用式(I)的化合物：（其中p为0至4；j为0至2；k为0至1；环A为芳基、杂环基、环烷基、环烯基、螺环基；环B为芳基、杂芳基；X为0或-NR7-；R1至R7和L为特定基团），该化合物的盐或该化合物或盐的溶剂化合物。
• Process for preparing spiro[indoline-3,4'-piperidine]s
  申请人：American Hoechst Corporation

  公开号：US04379932A1

  公开（公告）日：1983-04-12

  Novel spiro[indoline-3,4'-piperidine]s and related compounds and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants and tranquilizers. Also described is a novel method of preparing indoline rings.

  本发明涉及新型螺环[吲哚啉-3,4'-哌啶]和相关化合物以及其制备方法。这些化合物可用作抗抑郁、抗癫痫和镇静剂。还描述了一种新型吲哚啉环的制备方法。
• NOVEL 3-HYDROXYISOTHIAZOLE 1-OXIDE DERIVATIVES
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：US20130210721A1

  公开（公告）日：2013-08-15

  [Object] To provide a GPR40 activating agent containing, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the compound or the salt, or the like, particularly, an insulin secretagogue and a prophylactic and/or therapeutic agent against diabetes, obesity, or other diseases. [Means of Solving the Problem] A compound of Formula (I): (where p is 0 to 4; j is 0 to 2; k is 0 to 1; a ring A is an aryl group, a heterocyclic group, a cycroalkyl group, a cycroalkenyl group, a spirocyclic group; a ring B is an aryl group, a heteroaryl group; X is O or —NR 7 —; and R 1 to R 7 and L are specific groups), a salt of the compound, or a solvate of the compound or the salt.

  [目的] 提供一种GPR40激活剂，其中包含一种具有GPR40激动剂作用的新化合物作为活性成分，该化合物的盐、化合物或盐的溶剂合物等，特别是胰岛素分泌剂和预防和/或治疗糖尿病、肥胖症或其他疾病的药物。 [解决问题的方法] 公式(I)的化合物： 其中p为0至4；j为0至2；k为0至1；环A为芳基、杂环基、环烷基、环烯基、螺环基；环B为芳基、杂芳基；X为O或-NR7-；R1至R7和L为特定的基团，该化合物的盐或化合物或盐的溶剂合物。
• ONG, H. H.;PROFITT, J. A.;FORTUNATO, J.;GLAMKOWSKI, E. J.;ELLIS, D. B.;GE+, J. MED. CHEM., 1983, 26, N 7, 981-986
  作者：ONG, H. H.、PROFITT, J. A.、FORTUNATO, J.、GLAMKOWSKI, E. J.、ELLIS, D. B.、GE+

  DOI：——

  日期：——